Cis-4,5-didehydro-cis-13-PGA1 compounds

ABSTRACT

This invention comprises certain analogs of the prostaglandins in which the double bond between C-13 and C-14 is of the cis configuration. Also provided in this invention, are novel chemical processes and novel chemical intermediates useful in the preparation of the above prostaglandin analogs. These prostaglandin analogs exhibit prostaglandin-like activity, and are accordingly useful for the same pharmacological purposes as the prostaglandins. Among these purposes are blood pressure lowering, labor induction at term, reproductive-cycle regulation, gastric antisecretory action, and the like.

The present application is a divisional application of Ser. No. 595,869,filed July 14, 1975, now issued as U.S. Pat. No. 4,026,909 on May 31,1977.

The present invention relates to prostaglandin analogs for which theessential material constituting a disclosure therefor is incorporated byreference here from U.S. Pat. No. 4,026,909, issued May 31, 1977.

I claim:
 1. A compound of the formula ##STR1## wherein g is 2, 3, or 4;WHEREIN Y is cis-CH═CH-;wherein M₁ is ##STR2## wherein R₅ and R₆ arehydrogen or methyl, with the proviso that one of R₅ and R₆ is methylonly when the other is hydrogen; Wherein L₁ is ##STR3## or a mixture of##STR4## wherein R₃ and R₄ are hydrogen, methyl, or fluoro, being thesame or different, with the proviso that one of R₃ and R₄ is fluoro onlywhen the other is hydrogen or fluoro; Wherein m is 1 to 5, inclusive;and Wherein R₁ is hydrogen, alkyl of 1 to 12 carbon atoms, inclusive,cycloalkyl of 3 to 10 carbon atoms, inclusive, aralkyl of 7 to 12 carbonatoms, inclusive, phenyl, phenyl substituted with 1, 2, or 3 chloro oralkyl of 1 to 3 carbon atoms, inclusive, or a pharmacologicallyacceptable cation.
 2. A compound according to claim 1, wherein g is 4.3. A compound according to claim 2, wherein m is
 3. 4. A compoundaccording to claim 3, wherein at least one of R₃ and R₄ is fluoro.
 5. Acompound according to claim 4, wherein R₃ and R₄ are both fluoro.
 6. Acompound according to claim 5, wherein R₅ and R₆ are hydrogen. 7.15-EPI-2A,2B-Dihomo-16,16-difluoro-cis-4,5-didehydro-cis-13-PGA₁, methylester, a compound according to claim
 6. 8. A compound according to claim3, wherein at least one of R₃ and R₄ is methyl.
 9. A compound accordingto claim 8, wherein R₃ and R₄ are both methyl.
 10. A compound accordingto claim 9, wherein R₅ and R₆ are both hydrogen. 11.15-epi-2a,2b-Dihomo-16,16-dimethyl-cis-4,5-didehydro-cis-13-PGA₁, methylester, a compound according to claim
 10. 12. A compound according toclaim 3, wherein R₃, R₄, and R₅ are hydrogen. 13.15-epi-2a,2b-Dihomo-cis-4,5-didehydro-cis-13-PGA₁, methyl ester, acompound according to claim
 12. 14. A compound according to claim 1,wherein g is
 2. 15. A compound according to claim 14, wherein m is 3.16. A compound according to claim 15, wherein at least one of R₃ and R₄is fluoro.
 17. A compound according to claim 16, wherein both R₃ and R₄are fluoro.
 18. A compound according to claim 17, wherein R₅ and R₆ arehydrogen.
 19. 15-epi-16,16-Difluoro-cis-4,5-didehydro-cis-13-PGA₁,methyl ester, a compound according to claim
 18. 20. A compound accordingto claim 15, wherein at least one of R₃ and R₄ is methyl.
 21. A compoundaccording to claim 20, wherein R₃ and R₄ are both methyl.
 22. A compoundaccording to claim 21, wherein R₅ and R₆ are hydrogen. 23.15-epi-16,16-Dimethyl-cis-4,5-didehydro-cis-13-PGA₁, methyl ester, acompound according to claim
 22. 24. A compound according to claim 15,wherein R₃, R₄, and R₅ are hydrogen. 25.15-epi-cis-4,5-didehydro-cis-13-PGA₁, methyl ester, a compound accordingto claim 24.